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Compounds

COMPOUND NPA027369

STRUCTURE
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EXTERNAL LINKS
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PROPERTIES
NPAID NPA027369
CLUSTER ID 3672
NODE ID 2760
NAME Bisebromoamide
FORMULA C51H72BrN7O8S
MOLECULAR WEIGHT (Da) 1023.1490
ACCURATE MASS (Da) 1021.4346
ORIGIN ORGANISM TYPE Bacterium
ORIGIN GENUS Lyngbya
ORIGIN SPECIES sp.
InChIKey XNEWSWFKSIOKDS-NMKCGMRTSA-N
InChI InChI=1S/C51H72BrN7O8S/c1-12-41(60)37-19-16-22-58(37)46(64)39(26-33-17-14-13-15-18-33)57(11)45(63)36(23-30(2)3)54-49(67)51(9)29-68-43(55-51)38-24-31(4)28-59(38)47(65)40(27-34-20-21-42(61)35(52)25-34)56(10)44(62)32(5)53-48(66)50(6,7)8/h13-15,17-18,20-21,25,30-32,36-40,61H,12,16,19,22-24,26-29H2,1-11H3,(H,53,66)(H,54,67)/t31-,32-,36+,37-,38-,39-,40+,51+/m0/s1
SMILES CCC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)N(C)C(=O)[C@@H](CC(C)C)NC(=O)[C@@]1(C)CSC([C@@H]2C[C@H](C)CN2C(=O)[C@@H](CC2=CC(Br)=C(O)C=C2)N(C)C(=O)[C@H](C)NC(=O)C(C)(C)C)=N1
ORIGINAL ISOLATION REFERENCE
CITATION Teruya T; Sasaki H; Fukazawa H; Suenaga K Bisebromoamide, a potent cytotoxic peptide from the marine cyanobacterium Lyngbya sp.: isolation, stereostructure, and biological activity. Organic Letters 2009 11 (21) 5062-5065.
DOI 10.1021/ol9020546 PMID 19803465
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Bacteria LPSN 2
Phylum Cyanobacteria LPSN 1117
Class Cyanophyceae LPSN -
Order Oscillatoriales LPSN 1150
Family Oscillatoriaceae LPSN 1892254
Genus Lyngbya LPSN 28073
REVISIONS
VERSION SMILES CITATION
Original Isolation CCC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)N(C)C(=O)[C@@H](CC(C)C)NC(=O)[C@]1(C)CSC([C@@H]2C[C@H](C)CN2C(=O)[C@@H](CC2=CC(Br)=C(O)C=C2)N(C)C(=O)[C@H](C)NC(=O)C(C)(C)C)=N1 Teruya T; Sasaki H; Fukazawa H; Suenaga K Bisebromoamide, a potent cytotoxic peptide from the marine cyanobacterium Lyngbya sp.: isolation, stereostructure, and biological activity. Organic Letters 2009 11 (21) 5062-5065. DOI: 10.1021/ol9020546 PMID: 19803465
2 CCC(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)N(C)C(=O)[C@@H](CC(C)C)NC(=O)[C@@]1(C)CSC([C@@H]2C[C@H](C)CN2C(=O)[C@@H](CC2=CC(Br)=C(O)C=C2)N(C)C(=O)[C@H](C)NC(=O)C(C)(C)C)=N1 Gao, Xuguang; Liu, Yuqing; Kwong, Shuqin; Xu, Zhengshuang; Ye, Tao Total synthesis and stereochemical reassignment of bisebromoamide. Organic Letters 2010 12 (13) 3018-21. DOI: 10.1021/ol101021v PMID: 20527927
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